Bakuchiol

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Bakuchiol
Bakuchiol.svg
Names
Preferred IUPAC name
4-[(1E,3S)-3-Ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol
Other names
(+)-Bakuchiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.211.101 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 685-515-4
PubChem CID
UNII
  • InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1 Yes check.svgY
    Key: LFYJSSARVMHQJB-QIXNEVBVSA-N Yes check.svgY
  • InChI=1/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1
    Key: LFYJSSARVMHQJB-QIXNEVBVBX
  • Oc1ccc(/C=C/[C@@](\C=C)(C)CC\C=C(/C)C)cc1
Properties
C18H24O
Molar mass 256.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Bakuchiol is a meroterpenoid (a chemical compound having a partial terpenoid structure) in the class terpenophenol. [1]

Contents

It was first isolated in 1966 by Mehta et al. from Psoralea corylifolia seed and was called Bakuchiol based on the Sanskrit name of the plant, Bakuchi. [2] Bakuchiol is a meroterpene phenol abundant in [3] and mainly obtained from the seeds of the Psoralea corylifolia plant, [4] [5] [6] which is widely used in Indian Ayurveda [7] to treat a variety of diseases. [8] It has also been isolated from other plants, such as P. grandulosa, [9] [10] P. drupaceae, [11] Ulmus davidiana, [12] Otholobium pubescens, [13] Piper longum [14] and Aerva sangulnolenta Blum. [15]

Even though the first complete synthesis of Bakuchiol was described in 1973, [16] its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol A by Sytheon Ltd. [17]

It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with resveratrol. [18] One study in rats suggested that Bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss. [19]

Bakuchiol possesses antioxidant, [20] [21] anti-inflammatory (in mice), [22] [23] and in vitro antibacterial [24] properties. Bakuchiol isolated from P. corylifolia has shown activity against numerous Gram-positive and Gram-negative oral pathogens. It was able to inhibit the growth of Streptococcus mutans under a range of sucrose concentrations, pH values and in the presence of organic acids in a temperature-dependent manner and also inhibited the growth of cells adhered to a glass surface. [25]

Despite having no structural resemblance to retinol, [26] Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression. [27] [28] In 2018, a randomized, double-blind, 12-week clinical study with 44 volunteers demonstrated that Bakuchiol is comparable with retinol in its ability to improve photoaging (wrinkles, hyperpigmentation) but has a better skin tolerance. [29]

Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation. [30]

See also

Related Research Articles

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References

  1. ↑ J. Elks; C. R. Ganellin (1990). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 120–. ISBN   978-1-4757-2085-3.
  2. ↑ Mehta, G.; Nayak, U.Ramdas; Dev, Sukh (January 1966). "Bakuchiol, a novel monoterpenoid". Tetrahedron Letters. 7 (38): 4561–4567. doi:10.1016/s0040-4039(00)70078-5. ISSN   0040-4039.
  3. ↑ Chaudhuri, R. K.; Bojanowski, K. (2014). "Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects" . International Journal of Cosmetic Science. 36 (3): 221–230. doi:10.1111/ics.12117. PMID   24471735. S2CID   20823803.
  4. ↑ Banerji, A; Chintalwar, G (1983). "Biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia". Phytochemistry. 22 (9): 1945–1947. Bibcode:1983PChem..22.1945B. doi:10.1016/0031-9422(83)80019-3. INIST   9311490
  5. ↑ Cho, Hyun; Jun, Jung-Yang; Song, Eun-Kyoung; et al. (2001). "Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells". Planta Medica. 67 (8): 750–751. doi:10.1055/s-2001-18347. PMID   11731920. S2CID   260279217.
  6. ↑ Manohar, B.; Divakar, S.; Udaya Sankar, K (2009). "Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide". Bulletin of the Korean Chemical Society. 30 (8): 1760–1766. doi: 10.5012/bkcs.2009.30.8.1760 . INIST   22343814
  7. ↑ Does it make skin look younger?
  8. ↑ Koul, B.; Taak, P.; Kumar, A.; Kumar, A.; Sanyal, I. (2019). "Genus Psoralea: A review of the traditional and modern uses, phytochemistry and pharmacology". Journal of Ethnopharmacology. 232: 201–226. doi:10.1016/j.jep.2018.11.036. PMC   7127090 . PMID   30521980.
  9. ↑ Labbé, Cecilia; Faini, Francesca; Coll, Joseph; Connolly, Joseph D. (July 1996). "Bakuchiol derivatives from the leaves of Psoralea glandulosa". Phytochemistry. 42 (5): 1299–1303. Bibcode:1996PChem..42.1299L. doi:10.1016/0031-9422(96)00144-6. ISSN   0031-9422.
  10. ↑ Nadine Backhouse, C; Delporte, Carla L; Negrete, Rosa E; Erazo, Silvia; Zuñiga, Alexandra; Pinto, Alvaro; Cassels, Bruce K (November 2001). "Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities". Journal of Ethnopharmacology. 78 (1): 27–31. doi:10.1016/s0378-8741(01)00309-9. ISSN   0378-8741. PMID   11585684.
  11. ↑ Lystvan, Kateryna; Belokurova, Valeria; Sheludko, Yuriy; Ingham, John L.; Prykhodko, Valeria; Kishchenko, Olena; Paton, Evgenija; Kuchuk, Mykola (2009-12-20). "Production of bakuchiol by in vitro systems of Psoralea drupacea Bge". Plant Cell, Tissue and Organ Culture. 101 (1): 99–103. doi:10.1007/s11240-009-9657-0. ISSN   0167-6857. S2CID   10481048.
  12. ↑ Choi, Sang Yoon; Lee, Sanghyun; Choi, Won-Hee; Lee, Yeonmi; Jo, Youn Ock; Ha, Tae-Youl (August 2010). "Isolation and Anti-Inflammatory Activity of Bakuchiol from Ulmus davidiana var. japonica". Journal of Medicinal Food. 13 (4): 1019–1023. doi:10.1089/jmf.2009.1207. ISSN   1096-620X. PMID   20553183.
  13. ↑ Krenisky, Joann M.; Luo, Jian; Reed, Michael J.; et al. (1999). "Isolation and Antihyperglycemic Activity of Bakuchiol from Otholobium pubescens (Fabaceae), a Peruvian Medicinal Plant Used for the Treatment of Diabetes". Biological & Pharmaceutical Bulletin. 22 (10): 1137–1140. doi: 10.1248/bpb.22.1137 . PMID   10549873. INIST   1198639
  14. ↑ Ohno, Osamu; Watabe, Taeko; Nakamura, Kazuhiko; Kawagoshi, Masaru; Uotsu, Nobuo; Chiba, Tomohiro; Yamada, Masayoshi; Yamaguchi, Kohji; Yamada, Kaoru (2010-07-23). "Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated from Piper longumon Melanin Production in B16 Mouse Melanoma Cells". Bioscience, Biotechnology, and Biochemistry. 74 (7): 1504–1506. doi:10.1271/bbb.100221. ISSN   0916-8451. PMID   20622433. S2CID   12449051.
  15. ↑ "Aerva Sanguinolenta (L.) Blume, Extract 116425-35-5", Sax's Dangerous Properties of Industrial Materials, John Wiley & Sons, Inc., 2012-10-15, pp. 1–2, doi:10.1002/0471701343.sdp26534, ISBN   978-0-471-70134-7
  16. ↑ Damodaran, N.P.; Dev, Sukh (January 1973). "Meroterpenoids—III". Tetrahedron. 29 (9): 1209–1213. doi:10.1016/0040-4020(73)80103-6. ISSN   0040-4020.
  17. ↑ Chaudhuri, Ratan (2015-09-18), Sivamani, Raja; Jagdeo, Jared; Elsner, Peter; Maibach, Howard (eds.), "Bakuchiol: A Retinol-Like Functional Compound, Modulating Multiple Retinol and Non-Retinol Targets", Cosmeceuticals and Active Cosmetics, Third Edition, CRC Press, pp. 1–18, doi:10.1201/b18895-2 (inactive 2024-11-11), ISBN   978-1-4822-1416-1 , retrieved 2019-08-02{{citation}}: CS1 maint: DOI inactive as of November 2024 (link)[ permanent dead link ]
  18. ↑ Chen, Zhe; Jin, Ke; Gao, Lingyan; et al. (2010). "Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line". European Journal of Pharmacology. 643 (2–3): 170–9. doi:10.1016/j.ejphar.2010.06.025. PMID   20599920.
  19. ↑ Lim, Sun-Hye; Ha, Tae-Youl; Kim, Sung-Ran; et al. (2008). "Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague–Dawley rats". British Journal of Nutrition. 101 (7): 1031–1039. doi: 10.1017/S0007114508066750 . PMID   18801207.
  20. ↑ Adhikari, S.; Joshi, R.; Patro, B. S.; Ghanty, T. K.; Chintalwar, G. J.; Sharma, A.; Chattopadhyay, S.; Mukherjee, T. (September 2003). "Antioxidant Activity of Bakuchiol: Experimental Evidences and Theoretical Treatments on the Possible Involvement of the Terpenoid Chain". Chemical Research in Toxicology. 16 (9): 1062–1069. doi:10.1021/tx034082r. ISSN   0893-228X. PMID   12971793.
  21. ↑ Haraguchi, Hiroyuki; Inoue, Junji; Tamura, Yukiyoshi; Mizutani, Kenji (2002). "Antioxidative components of Psoralea corylifolia (Leguminosae)". Phytotherapy Research. 16 (6): 539–544. doi:10.1002/ptr.972. ISSN   0951-418X. PMID   12237811. S2CID   27269600.
  22. ↑ Ferrándiz, María Luisa; Gil, Blanca; Sanz, María Jesús; Ubeda, Amalia; Erazo, Silvia; González, Ernesto; Negrete, Rosa; Pacheco, Sergio; Payáa, Miguel (September 1996). "Effect of Bakuchiol on Leukocyte Functions and Some Inflammatory Responses in Mice". Journal of Pharmacy and Pharmacology. 48 (9): 975–980. doi:10.1111/j.2042-7158.1996.tb06016.x. ISSN   0022-3573. PMID   8910867. S2CID   25409612.
  23. ↑ Nadine Backhouse, C; Delporte, Carla L; Negrete, Rosa E; Erazo, Silvia; Zuñiga, Alexandra; Pinto, Alvaro; Cassels, Bruce K (November 2001). "Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities". Journal of Ethnopharmacology. 78 (1): 27–31. doi:10.1016/s0378-8741(01)00309-9. ISSN   0378-8741. PMID   11585684.
  24. ↑ Katsura, H.; Tsukiyama, R.-I.; Suzuki, A.; Kobayashi, M. (2001-11-01). "In Vitro Antimicrobial Activities of Bakuchiol against Oral Microorganisms". Antimicrobial Agents and Chemotherapy. 45 (11): 3009–3013. doi:10.1128/aac.45.11.3009-3013.2001. ISSN   0066-4804. PMC   90775 . PMID   11600349.
  25. ↑ Parimala Devi B, Ramasubramaniaraj R (2009). "Dental Caries and Medicinal Plants – An Overview". Journal of Pharmacy Research. 2 (11): 1669–1675.
  26. ↑ Dhaliwal, S.; Rybak, I.; Ellis, S.R.; Notay, M.; Trivedi, M.; Burney, W.; Vaughn, A.R.; Nguyen, M.; Reiter, P.; Bosanac, S.; Yan, H. (2019). "Prospective, randomized, double-blind assessment of topical bakuchiol and retinol for facial photoageing". British Journal of Dermatology. 180 (2): 289–296. doi: 10.1111/bjd.16918 . hdl: 2027.42/147746 . ISSN   0007-0963. PMID   29947134. S2CID   49430951.
  27. ↑ Chaudhuri RK, Bojanowski K (2014). "Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects". International Journal of Cosmetic Science. 36 (3): 221–230. doi:10.1111/ics.12117. PMID   24471735. S2CID   20823803.
  28. ↑ Chaudhuri, R. K.; Bojanowski, K. (2014). "Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects" . International Journal of Cosmetic Science. 36 (3): 221–230. doi:10.1111/ics.12117. PMID   24471735. S2CID   20823803.
  29. ↑ Dhaliwal, S.; Rybak, I.; Ellis, S.R.; Notay, M.; Trivedi, M.; Burney, W.; Vaughn, A.R.; Nguyen, M.; Reiter, P. (February 2019). "Prospective, randomized, double-blind assessment of topical bakuchiol and retinol for facial photoageing". British Journal of Dermatology. 180 (2): 289–296. doi: 10.1111/bjd.16918 . hdl: 2027.42/147746 . ISSN   0007-0963. PMID   29947134.
  30. ↑ Miao L.; Ma S; Fan G; et al. (2013). "Bakuchiol inhibits the androgen induced-proliferation of prostate cancer cell line LNCaP through suppression of AR transcription activity". Tianjin Journal of Traditional Chinese Medicine. 30 (5): 291–293. doi:10.11656/j.issn.1672-1519.2013.05.13. original title: 补骨脂酚拮抗AR转录活性抑制雄激素诱导的前列腺癌细胞LNCaP的增殖
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